A Stereoselective Route toward Polyhydoxylated Piperidines. A Total Synthesis of (±)-Deoxymannojirimycin - Sorbonne Université
Journal Articles Organic Letters Year : 2005

A Stereoselective Route toward Polyhydoxylated Piperidines. A Total Synthesis of (±)-Deoxymannojirimycin

Abstract

A chemo-and stereoselective palladium-catalyzed amination of silylated butenediol dicarbonates has allowed for the introduction of a glycine moiety to obtain the desired functionalized epoxysilane. A stereoselective aldolization then delivered the piperidine ring which may be used as a precursor for the synthesis of a variety of polyhydroxylated azasugars. This efficient approach has been illustrated by the synthesis of 1-deoxymannojirimycin including a stereoselective reduction with LAH and a Tamao−Fleming oxidation of a C−SiMe2Ph bond.
Fichier principal
Vignette du fichier
Deoxymannojirimycin-OL2005.pdf (384.62 Ko) Télécharger le fichier
Origin Files produced by the author(s)

Dates and versions

hal-04227430 , version 1 (03-10-2023)

Identifiers

Cite

Cécile Boglio, Sebastian Stahlke, Serge Thorimbert, Max Malacria. A Stereoselective Route toward Polyhydoxylated Piperidines. A Total Synthesis of (±)-Deoxymannojirimycin. Organic Letters, 2005, 7 (22), pp.4851-4854. ⟨10.1021/ol051745i⟩. ⟨hal-04227430⟩
20 View
10 Download

Altmetric

Share

More